


Critical Fail

by Ttttrickster (iscatterthemintimeandspace)



Category: Supernatural
Genre: Dungeon Master! Charlie, Dungeons&Dragons AU, Human AU, M/M, nerd au
Language: English
Status: Completed
Published: 2019-10-14
Updated: 2019-12-29
Packaged: 2020-12-16 11:37:10
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,180
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21035618
Author URL: https://archiveofourown.org/users/iscatterthemintimeandspace/pseuds/Ttttrickster
Summary: Gabriel had never pictured himself playing Dungeons & Dragons, but Charlie’s cute neighbor might have him joining the party.





	1. Chapter 1

**Author's Note:**

> The campaign for this fics is "Dragon of Icespire Peak Adventure" - https://5e.tools/adventure.html#dip  
Dungeons & Dragons, D&D, their respective logos, and all Wizards titles and characters are property of Wizards of the Coast LLC in the U.S.A.
> 
> I just borrowed it for this fic.

Gabriel didn’t know how he let Charlie talk him into this. 

She’d casually mentioned in passing that she held her own Dungeons & Dragons campaign at her house, and that there was a cute new guy who had started coming. Next thing he knew, she’d made him a character sheet, and he was on his way to her house with a bag of Doritos and a case of beer. 

Gabriel shifted from foot to foot as he rang her doorbell, feeling like a kid picking up his date from their parents’ house. The door opened a couple moments later, Charlie bouncing as she opened the screen door. 

“Hey, I wasn’t sure if you were coming!” she exclaimed, taking the beer from him. “The others are in the living room.” 

Charlie headed into the kitchen to put the beer on ice, and Gabriel, his character sheet clutched in his sweaty hand, went into her living room. 

Charlie’s living room was much the same as it always was, with the exception of a round beat-up oblong card table and several fold-up chairs. The table was laden with objects including paper, pencils, dice, and on one end, a large paper folder covered in graphic art. Three people were seated around it: a slight Asian boy wearing a light blue button up, a blonde girl twirling a plastic knife between her fingers, and a gorgeous tall brunette boy, who was currently smiling at him. 

“You must be Gabriel,” he said, “Charlie said you’d be here. I’m Sam.” 

Gabriel was momentarily tongue-tied. “Yeah… I’m… uh… that’s me.” He stopped and took a breath. “Nice to meet you all.” 

“That’s Kevin,” Sam pointed to the other boy. “That’s Jo,” he indicted the girl. “Nice to meet you too.” He smiled and when Gabriel looked, he could have sworn he had dimples in his cheeks. 

He tried to think up a response, anything to recover from his earlier blunder, but at that moment, Charlie walked in with two beers, saving him from his own embarrassment. 

“Let’s get this party started,” Charlie said. She grinned, handing a beer to Gabriel. “It’s Gabe here’s first campaign, so let’s not go too hard on him, eh?” 

Gabriel sat down. Sam gave him a reassuring smile. “Can’t promise anything,” he teased. “But we’ll try.” 

Charlie sat down behind her screen. “Okay where were we? Hmm…aha here we are. The village of Saldonia… Iron Belly Inn… Jo, Kevin, Sam… why don’t you give Gabriel a quick overview of your characters?”

Kevin began. “I’m Vanconto Cennor, a human acolyte from Triboar, a small fishing town to the east of Phandalin. I came on a religious pilgrimage and stopped to help an innkeeper who was having a hard time with some goblins.” 

“Name’s Imendem Mora, a wood elf soldier from Neverwinter. I was separated from my battalion and came to  Phandalin looking for a way home,” Jo told him, with a glint in her eyes. Something told him she was the one to look out for. 

Sam looked over at him. “I’m playing as Lord Irieel of Mercuria,” he began. “An Aasimar noble who-” 

“A what now?” Gabriel asked. He’d read the copy of the manual that Charlie had given him, but there was just so much to learn, he’d hadn’t absorbed as much of it as he would have liked. “Sorry” 

.

“No big deal,” Sam said, trying to reassure him. “The Aasimar are a humanoid race, descended from angels. Like nephilim from the Bible?” 

Gabriel shrugged. “I haven’t read the Bible much,” he quipped, with a small smirk. “But I’ll take your word for it.” 

Sam cleared his throat. “You’re welcome. As I was saying, Aasimar noble from the Kingdom of Mercuria, who ended up in Phandalin after his ship crashed off the coast. He’s trying to earn enough money to book passage home.” 

“What about you, Gabe?” Charlie nudged, looking at him over her screen. 

Gabriel looked down at his character sheet. Charlie had said he had to come up with a backstory for his character, but of course he hadn’t done that so he just improvised. “I… I’m Tila the Green, a gnome charlton from… Conyberry… where I was run out of town for seducing the magistrate's daughter,” he added with a smirk. “And taking her dowry with me.” 

Charlie nodded in approval. “Nice backstory,” she said. “Now where were we? Ah yes, your company is on the way to Butterskull Ranch, in pursuit of a white dragon that has been wreaking havoc on the local villagers. Your company chose to take the Triboar Train, the safer but longer way to the ranch.” she noted. “Up head you see the ruins of a small village, it seems abandoned, but you can hear movement from behind one of the buildings…” 

Initially when Charlie had talked him into this, Gabriel had been hesitant. He doubted his abilities to be able to improvise at the drop of a hat., but as the night wore on, and he got used to the ebb and flow of the game, he found himself getting more and more into it. He even got a couple laughs from the rest of party along the way. 

“As you make your way across uneven ground rising to a ridge, several hulking orcs ascend a similar ridge across from you, separated from you by a sixty-foot-wide, ten-foot-deep gully. The orcs unleash terrible battle cries as they are joined by a humanoid with elongated claws,” Charlie said, her eyes scanning the page in front of her. “Lead by Yargath, an anchorite of Talos.”

Gabriel had no idea what that was, but he understood orcs. He had watched Lord of the Rings, after all. They couldn’t be all that different. 

“So how many orcs are chasing us?” he asked Charlie, looking over his character sheets for a means of escape. 

“Six,” Charlie replied, glancing at each of them in turn. “They seem to all be carrying clubs. Yargath casts a blessing on the three orcs closest to him. They charge across the ravine and seem to be in melee range, Jo, what do you want to do?” 

“I take out my battleaxe,” Jo began, “And attack the closest Orc,” 

“Roll for damage,” Charlie told her, rolling a set of dice behind her paper screen. 

Jo rolled her D20 and grinned up at Charlie when she saw the number. “17, plus by modifier is 21.” 

“You hit and deal 7 damage, he falls to the ground, gravely injured but not dead,” she narrated. “Vanncoto, your turn next.” 

Kevin looked back down at his sheet. “How close to me is Yargath?” 

Charlie consulted her map. “About 20 feet.” 

“I cast my flame cantrip at Yargath,” Kevin said, picking up his D20. He rolled it onto the mat in front of him. “Ten, plus my modifier makes eleven.” 

“Roll your d8 for flame damage.” 

Kevin picked up his eight-sided die and shook it up in his hands, letting it go with a flourish. “Three,” he told Charlie. 

“Three points of fire damage for Yargath,” Charlie said. “ Irieel, you’re up next. What do you want to do?” 

Sam gave Gabriel a shy smile, and then looked down at his sheet quickly. “I take out my cross bow and target Yargath.” 

“Roll,” Charlie commanded, as she rolled for Yargath. 

Sam did was he was told, rolling his D20, but he grimaced. “Fuck, four.” he hung his head a little, his hair coming to rest over his face. 

“You miss him,” Charlie replied. “The orcs are advancing rapidly; charging at you, they’re only ten feet away now, save for the guy that Jo took out. Tila?” 

Gabriel took a deep breath. His character wasn’t very good at fighting, and he wasn’t particularly good at rolling, but he figured that as a charlatan, he should have something up his sleeve. FInally his eyes lighted on it. 

“I take a bag of ball bearings from my bag,” Gabriel started with a smirk. “And empty them into the path of the orcs.” 

Jo, Kevin, Sam and Charlie all turned to look at him. “Roll for that,” Charlie said, watching him with interest. 

Gabriel carefully picked up his D20,and rolled it around in his hands. He closed his eyes and released the die onto the table. 

He didn’t want to open his eyes, almost didn’t want to now, but he heard a whoop and opened them. He couldn’t believe it. 

He’d rolled a natural 20. 

His eyes shot up to Charlie, who was staring at him with disbelief. She picked up the die she had rolled to show him. It had rolled a 1. Critical fail. 

“The orcs and Yargath trip and fall on your ball bearings,” Charlie said, finding her voice again. “Ashamed and humiliated, they slink off into the forest, never to be seen again.” She offered a smile. “And that’s where we’ll stop for tonight. Great session, guys!” 

Kevin and Jo began collecting their things, putting all their dice into bags, and slipping their character sheets into folders. 

“Sammy, I’m going to give Kevin a ride home. You want one, or you gunna walk it?” Jo asked, taking her keys out of her backpack. 

Sam was just finishing packing up his stuff, and he gave Gabriel a quick glance over his shoulder. “I’ll walk, it’s a beautiful night.” 

“Charlie didn’t mention you living so close to her,” Gabriel said, pulling his bag over his shoulder. “I only live on Larkspur.” he began to walk towards the door. “Where do you live?” 

“I’m over on Crescent,” Sam told him, rising to his full height. Gabriel didn’t think he’d fully appreciated it before, and suddenly he was consumed with a crazy idea. 

“Can… can I walk you home?” Gabriel burst out, unable to contain himself. “Wouldn’t want the orcs to get you.” 

Sam blinked at him and for a moment, Gabriel thought he was going to be banned from the group already, but Sam surprised him. 

“I’d love that.” 


	2. Chapter 2

**Summary for the Chapter:**

> Gabriel's enjoying D&D a lot more than he would.

**Notes for the Chapter:**

> I apologize for any errors. This chapter is un-betaed.

Gabriel couldn’t stop thinking about Sam. 

Their walk home had been nothing but ordinary, but Gabriel was already hooked. 

They’d only talked, Sam explaining the finer points in the game in great detail, his face shining with excitement. He didn’t scoff at Gabriel when he asked what was surely a stupid question, taking the time to respond in a way a novice player like Gabriel could understand. 

What was a ten minute walk seemed the stretch hours as Sam spoke, each word hanging abundantly in the air between them, Gabriel stuck on every one of them. 

“Well this is me,” Sam said finally, hiking his thumb over his shoulder at a small house set back towards the woods. “It’s been really nice talking with you. I’ll see you next week!” 

He spun on his heel with a smile and headed back towards his house, leaving Gabriel in his wake. “I’ll - I’ll pick you up?” 

Sam stopped and for a moment, Gabriel thought he was going to get rejected, but Sam turned halfway around. “I’d really like that.” 

He went to continue his path down the drive away, still looking over his shoulder at Gabriel as he walked. Sam started to wave back at him, but then tripped over his own two feet, sending him quickly to the pavement. 

Gabriel took a step forward, meaning to help him up. Sam popped back up, almost as quickly as he had fallen, his face as red as a tomato. He gave an awkward little wave, and then headed back to his house 

The week had crawled by as Gabriel counted down until their next session. He knew he could always ask Charlie for Sam’s number, but he didn’t want to come on too strong. He didn’t even know if Sam was single yet, let alone into guys. So he waited. 

Finally, the day came and Gabriel took two showers and changed his outfit three times before he made his way over to Sam’s. 

He found Sam waiting on his porch, thumbing through the player’s manual. He smiled up at Gabriel when Gabriel called his name. 

“Hey Gabe,” Sam said, closing the book and putting it away in his bag. . “How was your week?” 

“Flew by,” Gabriel lied to him, shoving his hands into his pockets. “How about you?” 

Sam shrugged as he stood up. “Same was always. Work, class, more work.” 

“Class?” Gabriel asked him. “Are you in grad school?” 

“Law school. I have one more year left, and I’ve been working as a paralegal with Legal Aide.” Sam replied. He pushed his hair out of his face as he spoke. 

Of course Sam would be studying something like law, Gabriel thought to himself. He was so clever and well-spoken during their campaign, it didn’t surprise him that he was smart in real life too. 

They chattered back and forth until they reached Charlie’s house. Sam rap smartly on the door, and eventually Charlie poked her head out. She looked like hell. There were dark bags under her eyes and she had the distinct look of someone who’d just woken up. 

“Fuck guys, I’m sorry.,” Charlie said, her voice sounding stuffed up. “I completely forgot to text you guys. I have the flu.” 

Both Gabriel and Sam took a step back. 

“That’s okay,” Sam said. “Feel better, we’ll see you next week.” 

Charlie closed the door, and both men turned to leave. 

“Guess I’ll go back home,” Sam looked over at Gabriel sadly. 

“We don’t have to go home,” Gabriel seized the opportunity. “We’re already out, want to grab lunch?” 

Sam looked over at him and for a moment, Gabriel thought he was going to say no, but he didn’t. 

“I’d like that,” Sam smiled at him. “Where do you want to go?” 

“Uhhh,” Gabriel hadn’t thought that far ahead. The choice to ask Sam to lunch had been made in a split second, to keep Sam from going home, to spend more one on one time with him. “Surprise me.” 

They ended up at a dim sum restaurant that Sam swore up and down as the best he’d ever had, and so he trusted him. He’d never been to a dim sum before, and the whole experience was odd, but Gabriel found that he liked it. Carts that brought him dish after dish of tasty Chinese food? Sign him up. 

They sat across from each other in a dark corner booth, Sam explaining each dish as it came piping hot from the cart. 

“So what’s this one?” Gabriel asked, as the waitress put two small bowls on their table. There was a little envelope of rice noodles, filled with something lumpy and sprinkled with chives. 

Sam picked up one with his chopsticks and took a bite. “Rice roll, pork I think,” Sam saif through a mouthful of food. “It’s really good.” 

Gabriel took the remaining roll, and put the whole thing in his mouth without thinking. He regretted it a second later, when it burned both his tongue and the roof of his mouth. He chewed like a mad man, his mouth partially open. “Yeah,” he agreed. “Really good.” 

Sam laughed, and even though his mouth was burned so badly he most likely wouldn't be able to taste anything for a week, he found he didn’t mind so much. 

“So,” Gabriel started, as soon as he had swallowed. “How did you get into D&D?” 

“We’ve moved around a lot when I was a kid,” Sam told him, laying his chopsticks to the side. “I was always the new kid in school, I didn’t have any friends, but I did have books.” He looked up. “Dean found the Player’s Manuel at a thrift store and got it for me. I practically memorized the thing. Pretty sad, huh?”

Gabriel shook his head. “I don’t think so,” he said. “It’s sweet. Books were my escape too. Whenever my brothers were mean to me, I would take a book and hide in the laundry room until my mom found me.”

He’d never shared that particular fact with anyone except Charlie and for a moment, Gabriel felt shame warm his cheeks. He and Sam didn’t know each other very well, had he overstepped the boundaries ? 

Sam smiled at that. “Im glad I’m not the only one.” 

They continued to talk and laugh until it was time to go. Gabriel didn’t want it to end, but he couldn’t very well keep Sam to himself forever. 

Sam and Gabriel walked back the way they came, with significantly fuller bellies, but Gabriel was dreading each step closer to Sam’s house. He knew he would see him next week, but that would be in the company of the rest of the party. 

“Gabriel? You okay?” 

Gabriel startled. They’d stopped in front of Sam’s house and Sam was looking at him with a concerned look on his face. “Yeah, sorry Sammy,” he apologized sheepishly. “Just distracted, that’s all.” 

“Anything I can help with?” Sam asked. 

Gabriel glanced up at him. “Uh Sammy. I...I really enjoyed this. Can we do it again sometime… as a date?” 

“Gabriel.. I…” 

Gabriel turned away. He didn’t want to hear the rest. He didn’t know what he was thinking, and now he’d ruined not only his friendship but their campaign as well. Charlie was going to be so mad at him when she found out...

“Gabe!” 

He turned back and was almost instantly blindsided by Sam’s lips pressed against his. All Gabriel could do was hold on for the ride. He felt Sam’s hands come up to cup his jaw, pulling him closer. 

When they finally pulled away, all Gabriel could say was “Wow, I was not expecting that.”

Sam pushed a lock of hair back from his face. “Is that a good thing or a bad thing?” 

“I just asked you out, and you’re asking me if it was a bad thing?” Gabriel’s eyebrow rose as he regarded Sam. “It’s a good thing, Sammy, but why do you look like someone just kicked your puppy?” 

“Charlie,” Sam said finally, not quite meeting his eyes. “She doesn’t want dating to make the campaign awkward. Did she tell you?” 

“She failed to mention that,” Gabriel replied. Leave it to Charlie, she wasn’t even here and she was cock-blocking him. “I didn’t mean to put you in a weird spot, kiddo.” 

“It’s not your fault,” Sam answered back, finally looking at him. “It’s a stupid rule anyway.” 

“No arguments from me there,” Gabriel agreed. “But rules are meant to be broken right?” 

Sam looked him over for a moment, and then a smile blossomed on his face like the sun rising over trees. “You’re right. Charlie doesn’t have to know.” 

Gabriel shared Sam’s smirk as a thought hit him. He leaned in closer to him, unable to keep a chuckle out of his voice. 

“Roll deception check.” 

Sam looked at him blankly for a moment, and then an incredulous look spread over his face. He pulled Gabriel in and kissed him again. 

“Nat20,” he said with a smile. “Critical hit.” 

**Author's Note:**

> Disclaimer: this may not be totally accurate. I’m a bee D&D player so I don’t have much Experience.


End file.
